Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: the synthesis of Semaxanib and GW441756

J Lubkoll, A Millemaggi, A Perry, RJK Taylor

Index: Lubkoll, Jana; Millemaggi, Alessia; Perry, Alexis; Taylor, Richard J.K. Tetrahedron, 2010 , vol. 66, # 33 p. 6606 - 6612

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Citation Number: 26

Abstract

A tandem sequence involving Horner–Wadsworth–Emmons (HWE) olefination followed by a palladium-catalysed intramolecular Heck reaction has been developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium (II) acetate or tetrakis (triphenylphosphine) palladium, and has been used to prepare a range of adducts derived from aromatic, ...